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<h1><a href="https://archiveofourown.org/works/26877223">Pretty Pink Princess Darwin</a> by <a class='authorlink' href='https://archiveofourown.org/users/PeeJayXela/pseuds/PeeJayXela'>PeeJayXela</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>The Amazing World of Gumball</td></tr>

<tr><td><b>Genre:</b></td><td>Come Inflation, F/M, Feminization, Grooming, Shaving, Shaving Kink, Stretched Hole, Trans Character, Trans Female Character, mild grooming</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-07</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-07</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 20:07:02</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Underage</td></tr>

<tr><td><b>Chapters:</b></td><td>2</td></tr>

<tr><td><b>Words:</b></td><td>3,276</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/26877223</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/PeeJayXela/pseuds/PeeJayXela</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>In feeling unsure of himself, Darwin approaches the new school councilor, hoping to see if he can help with Darwin's internal struggles. </p><p>It ends up that... she gets a lot more than she bargained for...</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Darwin Watterson/Original Male Character(s)</td></tr>

<tr><td><b>Kudos:</b></td><td>10</td></tr>

</table>

<a name="section0001"><h2>1. Chapter 1</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>“I… I’m going through something really weird, Mr Councillor, Sir…” Darwin said, looking up with big brown eyes to the man behind the desk, swallowing thickly. </p><p>Darwin’s legs tilted in, his knees hitting together, thighs barely touching. </p><p>The councillor stared at him silently, and he swallowed again, nervousness coursing through him in all kinds of ways. </p><p>Finally, the man in front of him spoke, a low tone that hit the back of the boy’s neck, running down his vertebrae. </p><p>“What seems to be the problem, Darwin.” The man said, clasping his big hands on the desk, leaning forward into it. </p><p>“Well… Uhm… It’s real weird, Mr Councillor, Sir- b-but lately, I uh… I’ve been feeling… Uhm… Kinda trapped in my own body… It’s all confusing but… Gumball says I’m going through… ‘Pubbety’ and that I’m gonna turn into a man- but…”</p><p>He looks down, tapping his toes together in nervousness, his sneakers feeling so uncomfortable… </p><p>“I don’t think I wanna be a man, Mr Counciller, sir.” The boy… well… the confused child said, visibly shaking now. </p><p>His big brown eyes looked back up at the counciller, almost brimming with tears. </p><p>And, with a sigh, the man nodded, standing up and grabbing a whiteboard pen, drawing a little picture of a person on the board. </p><p>“This is you.” He said, handing the pen to Darwin, and standing back. </p><p>“Draw what you want to look like, on the board.” He said, stepping away from the whiteboard and letting the other grab the pen.</p><p>So, the child grabbed the pen, hopping up on the chair (For he was so, so short) and stood, holding the pen above the stick figure. </p><p>And… they drew. He put little heels on his feet, a poofy dress on his body, and drawing nice long hair…. </p><p>It seemed that Darwin’s view of femininity seemed to be… princessy? Which made sense- they were only young, feminine idols was pretty much… Mom, and video games. </p><p>Darwin looked around, incredibly nervous, and looking for the opinion of the councillor in front of him…</p><p>But, thankfully, the councillor nodded, pulling Darwin off the chair by under the armpits, plopping them down.</p><p>“Well… We can dress you up like that, and see if you like it?” He said, making Darwin incredibly nervous, his stomach knotting up. </p><p>“Why are you nervous?” The man asked, leaning over Darwin. </p><p>“Stay here, I’ll go and see what we have, see what we can make you look pretty with.” He said, a grin over his face. </p><p>Almost a leer, and the way the councillor said ‘Pretty’ made Darwin’s insides squirm…</p><p>But the man went off, and Darvin was left to sit and squirm on the student bench, swinging his legs as he waited for the man to return… </p><p>Or… hers…? Theirs? </p><p>Oh, it was all making him… them… her… so confused… </p><p>Still, the Councillor came back around ten minutes later, holding some fabric, and shoes, and… hair…? </p><p>He came in and closed the door, pulling down the little curtain so nobody could see in… which was… fishy, if you’ll pardon the pun… </p><p>The councillor put the things down on the dress, and when Darwin got up to approach, to look, his eyes SHONE. </p><p>Little eager hands reached into the chiffon, pushing the netting and looking at the petticoats that came with it.</p><p>He- SHE, was so happy, little eyes gazing up in wonderment at the councillor. </p><p>“Can I… put ‘em on?” She asked gently, trembling in excitement at the idea of looking so… pretty…?</p><p>Her face lit up in a happy expression when the man nodded, and reached to grab as much fabric as she could, but the man's hand reached out to stop her. </p><p>“Here, let me help you.” He said, squatting down to help Darwin take off her old... boys clothes. </p><p>There was hesitation, nervousness on Darwin’s end, stepping back and covering her chest, going a shade of red. </p><p>“W...Wait… you’re gonna help me… change?” She asked, looking at all the dresses and pretty pink things she desperately wanted to dress in. </p><p>The man nodded, giving a smile. “Yeah. It’s gonna be difficult to get that dress and wig on by yourself.” He told her, picking up the dress and showing the ruffles and such. </p><p>Darwin looked at it, and at the wig, and took a long exhale, then a smile. </p><p>“Okay- Yeah, you’re right!” She smiled, brown eyes still nervous, but a lot happier. </p><p>She held her arms up in the air as the councillor squatted down to pull her boy shirt over her head, tossing the orange shirt far away, way into the past. </p><p>It felt… good, and free, to have her old shirt thrown away, like a burning of her old mask- She was… happy, and more confident to have the rest of her clothes taken away by this man helping her. </p><p>So, she let him, letting him take off her shoes, and jeans, and leaving her in her boxers, black with little orange fish all over them. </p><p>The councillors hands reached for those, and Darwin put down a hand to stop him, once again nervous about being undressed. </p><p>“I’m not going to hurt you.” The man said, once more hooking his thumbs into the orange waistband, and Darwin took a deep breath. </p><p>“It’s okay, I got some underwear for you, too.”</p><p>Where…. Did he get girls underwear? </p><p>Before Darwin had a chance to question that, her boxers were pulled down, and she yelped, cupping her hands over her private parts-</p><p>The man pulled back, smiling widely at the nude boy- something that was a little creepy, but Darwin just looked away, dark cheeks red. </p><p>“Ca-Can I put the dress on now, Mr Councillor, Sir?” She asked, looking wistfully to the frilly dress on the desk. </p><p>With a nod, the man reached to grab it, bunching the petticoats and underskirts into his fists, holding it over the young girls head. </p><p>“Raise your hands.” He said, and Darwin complied. </p><p>As the man pushed the dress over the girl, his eyes drifted to her momentarily uncovered groin before it was covered from view. </p><p>Still, Darwin looked down at herself, eyes absolutely sparkling upon seeing her legs in the skirt, her waist in the- </p><p>“HEUGH-” She yelped, looking back to see the man behind her pulling the corset of the dress tight, pulling her waist in, feminine, cinched- </p><p>It squeezed the breath from her lungs, but when she looked down at her new tiny waist, she was so, so happy, a grin spreading over her face and giving a twirl as soon as the man had finished tying her waist all small and feminine. </p><p>She was so happy, giving another twirl- </p><p>A small breeze wafted under her, and she realised the skirt was much smaller than she thought, but that was okay- she was going to put on nice pretty panties too, right?</p><p>She looked up at the man, who gestured to a seat, and Darwin sat down obediently in it, giving a “What are we doing now?” </p><p>The man smiled at her, bringing out a comb and lots of little hairbands. </p><p>“We need to smooth down that pretty hair of yours to put the wig on.” He said, and Darwin nodded, swinging her pretty legs under the chair. </p><p>So, without further ado, Darwin’s natural, thick full afro was slowly combed out, slowly teased to lovely chocolate curls, and started to braid them to her head, nice and small and dense against her scalp. </p><p>Finally, all her hair was braided and put into a low bun, and the wig was brushed down and gently pushed over the braids, pinning and gluing the hem down, making sure it wouldn’t move at all, no matter how much yanking or tugging. </p><p>Darwin reached to her new hair, running her hands through the silky blonde locks, letting out a happy little sigh at her princess hair, shaking the bangs in front of her face. </p><p>“I’ve got white people hair.” She giggled at the councillor, but seemed happy either way. </p><p>She shook her head again, feeling all the soft, ribbon like hair cascading down her neck. </p><p>While she was busy with that, the man had grabbed her tiny ankles, sliding the pretty pink heels onto her feet, doing up the ankle straps. </p><p>She gasped, immediately trying to stand up, and wobbling, falling into the man’s arms, who caught and held her by the waist, causing an extreme blush to dust over her cheeks, deep and red… </p><p> </p><p>“You look pretty…” The man said, standing the girl up and letting her get her balance, sticking her hands out like a princess taking eloquence lessons. </p><p>The words went straight to her gut, taking little toddling steps, learning how to walk in these things, managing to get to the desk and tripping, leaning over the desk, chest flat against the wood. </p><p>Her skirt puffed up as she was folded over the desk, creating a halo of skirts and petticoats around her cute butt. </p><p>She had a lovely plump butt, two fat cheeks meeting in the middle to a dark hole and a pretty taint… </p><p>The councillor made a sound behind her, and she looked around to see his eyes staring, another deep blush over her face. </p><p>But… she didn’t stand up, or cover herself- she just kept her brown eyes looking back, a question swirling around her mind. </p><p> </p><p>“Do… I look like a girl, like this, Mr Councillor, sir?” She asked, legs shaking with the effort of standing just on her toes in these heels. </p><p>The man took a breath, and nodded, bringing a light, happy, fluttering feeling into her chest. </p><p>“But-” He added, and her happiness was deflated slightly. </p><p>“You still have boy hair-” He said, turning and going to his drawer, picking out a shaving kit that he used to teach concerned boys how to shave. </p><p>But today, he was going to use it for a very different reason.</p>
  </div></div>
<a name="section0002"><h2>2. Chapter 2</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>“I can get rid of it for you, Darwin… Do you still want to be called Darwin?” </p><p>The girl thought about both of those things for a moment, before nodding to both account, unsure, but having made a decision. </p><p>“You can get rid of the hair… And I still wanna be called Darwin.” </p><p>The man nodded, kneeling down and taking out the travel sized can of shaving cream, wetting his hand using his water bottle and smoothing shaving gel all over the girls legs, up her thighs, over her soft, supple cheeks… </p><p>He flipped the skirt up, smoothing up to the small of her back… </p><p> </p><p>Then, he started dragging the razor down the calf of the girl, long, slow drags, before pouring some water on the razor to clean in, and moving up to the thighs. </p><p>Shaving the thighs had a much more intense reaction, Darwin starting to tense and twitch, legs spreading slightly to allow the councillor to get to his inner thighs, each long stroke of the blades making her whine slightly. </p><p>Her ass, next, shaving from the small of her back down to her cheeks, to the top of her thighs, revealing deep dark smooth skin that squished under the gentle push of the razor blade against her thin dark hairs. </p><p>The councillor spread her cheeks, making her yelp, but not squirm, and rubbed some shaving gel over her hole, and balls, making her press her cheek against the desk and take long, fluttering breath. </p><p>“Can I shave here?” The councillor asked, despite the fact that he was already rubbing Darwin’s sensitive balls with shaving gel… </p><p>“Yes… Y-you can…” She said, spreading her legs a little bit more despite her ankles wobbling with the new angle of balance on her heels… </p><p>Without hesitation, the man ran the blade over the girls pretty puckered hole, watching it twitch and pulse under the attention, running all the way down to the balls, under the taint and gently cupping the little bulge, getting each nook and crevice. </p><p>She whined slightly, again, trying not to push back on the blade, because that would be painful… </p><p>But the man pulled away, and Darwin stood, looking down at her smooth new legs, like black barbie legs… </p><p>She let out a happy little laugh, reaching down to smooth her hands down her legs, her cheeks pink with delight… </p><p>“They’re so pretty..” She said, tearing up and letting tears roll down her face in utter happiness. </p><p>She lifted her skirts to look at her… privates, and frowned, turning to show the man ahread. </p><p>“Can you shave my front, too?” She asked, leaning back against the desk, showing her little happy trail, dark hairs making a little halo around her… hardness. </p><p>The Councillor stared, raising a brow at her, but said nothing to her as he washed off the razor, and started rubbing shaving gel over her lower tummy, down to the shaft and front of her soft balls. </p><p>Gently, he shaved down her trail, watching her breath hitch, cock twitch at the feel of the careful attention against her shaft… </p><p>When he finished, he looked up at her, and put a hand against her hard cock. </p><p>“You’re hard.” He said to her, standing up to look down at her, still cupping her private parts.</p><p>“From me shaving you? Or from being a girl…” He asked, and Darwin looked up with nervous eyes… </p><p>She thought about it for a moment, her brown eyes worried, but leaning into the man’s hand. </p><p>“I think… From you shaving me- or.. Maybe both..” She mumbled, thighs twitching to move against the hand once more. </p><p>“Is that bad? Am I not supposed to be hard if I’m a girl?” She asked, tears pricking her eyes once more. </p><p>But the man just chuckled, shaking his head, and moving his hand against her groin, making he breath hitch and flutter. </p><p>“No, it’s fine, but usually, girls like you get their… special time in a different way..” He said to her, making her head tilt. </p><p>“How do girl… How do girls like me have their...special time…? Gumball’s tried to make me do special time with him, but I… I don’t like touching it- even in front of him…”</p><p>The man tilted his head, before putting a hand on the girls waist, turning her around so she was leaning against the desk once again. </p><p>“They use… This part…” He told her, pressing a finger against her freshly shaved, puckered hole. </p><p>She quivered, her thighs tensing up and legs moving further apart, more room for the man to teach her.</p><p>“The… The poop hole?” She asked gently, but she couldn't deny that she was feeling a heat pooling in her gut. </p><p>He laughed, rubbing against the hole some more, listening to her gasps and whimpers… </p><p>“It can feel really good… It’ll make you feel like you have girl parts… would you like that?” He asked, his fingertip threatening to push in. </p><p>Darwin’s breath hitched, unable to form words, but nodding. </p><p>Finally, she spoke.</p><p>“P..Please make me a girl…” She said, perking her supple rear up more. </p><p>Again, without hesitation, the councillor pushed his finger in, shaving gel acting as lube as he felt the girl’s virgin insides as she gasped, groaned, moaned… </p><p>“Feels so strange…” She gasped, rutting her hips against the desk, trying to apply some friction to her special parts. </p><p>All the friction she needed would come soon, though, as the man behind her started to shove his finger in and out of her, making her reach her arms out in front of her, grabbing the other side of the desk and whining out in some kind of unsure pleasure… </p><p>He continues with her insides, pushing another gelled up finger, listening to her gasp out-</p><p>“S-stretch-!”</p><p>A laugh came from him, his free hand smoothing over her cinched waist, making her moan out, hopefully happy. </p><p>“You know, Darwin-” He smiled, scissoring his fingers inside of her, feeling for her tiny prostate, to get an aim for later. </p><p>“Lots of girls like to feel feminine by taking a man inside her. Something about mirroring heterosexuality.” </p><p>Darwin groaned, looking back at him with lidded, big brown eyes… </p><p>And nodded… </p><p>The man grinned, pulling back and unzipping himself from his pants, revealing a cock that was far too big for Darwin to take… </p><p>But it was too late now, and the man spread the others cheeks, revealing the pretty dark hole, twitching and winking- and clenching when the man’s fat tip pressed against her hole, throbbing just the same… </p><p>“Ah-! W-wait, too big-!” She yelped, before screaming out when the cock was pushed inside her, asspussy stretching out like an elastic band around his shaft. </p><p>“Oh god oh god oh god ngh-! Ffff- fuh… Frick…” She said, not brave enough to actually swear. </p><p>Her tummy was bulging out, the tummy bump hitting the desk, her own cock pressing against the tummy bulge. </p><p>“You ready…?” He asked, and Darwin looked back, tears streaming down her face, confused and pained…</p><p>“Ready for… wh-AGH~!”</p><p>She grabbed the end of the desk, burying her wet face against the desk and sobbing out as she was well and truly fucked in the ass, shoving her against the desk each and every time his hips jerked forward. </p><p>But, despite the crying and the pain, she was still very very hard, and between the cries and yells, she moaned and whimpered. </p><p>“You like this, Darwin?” He asked, leaning over her and grabbing her pretty blonde hair, balling it up in his fist and grunting as he tugged. </p><p>“I think you really like being filled up- it makes you just like a girl, Darwin… such a pretty girl, the prettiest girl I’ve ever fucked into a desk…” </p><p>Darwin moaned at all this praise, feeling feminine and wonderful and euphoric and- her dysphoria was almost all gone. </p><p>“Yeah? You like me calling you such a pretty girl… Pink and wonderful… Smooth legs and long hair and so, so pretty in a dress.” </p><p>She moaned again, all of those words going straight to his gut. </p><p>“C-close- ngh- I- I think I-” She mumbled, before her eyes widened, for the man behind her had grabbed her hips and push her competely onto the desk and continue to fuck her, but changing his angle to that his tip was shoving against her prostate each and every time he pushed into her. </p><p>She yelped, moaning and yelping out in utter pleasure as her sweet spot was absolutely abused, legs twitching and hooking up onto the desk to spread herself even further. </p><p>And- she came, spurting over the desk, over her stomach, sandwiched between the desk and her skirts, white liquid spurting over herself… </p><p>Soon after, after a few more harsh thrusts, he came, filling the girl up utterly and completely, lifting her off the desk a little from how big her belly bulge became. </p><p>He pulsed, the waves of cum eventually leaking from her hole, and he finally pulled out, letting the stream gush out of her… </p><p>She let out a long breath, finally relaxing…</p><p>“Do you feel good?” He asked, sitting back on his desk chair.</p><p>Darwin lay on the desk, fluttering her eyes shut, and nodding. </p><p>“Y..yeah, Mr Councillor, Sir… I.. I feel..”</p><p>“Do you feel like a girl?” He asked, reaching forward to pull the girl into his lap, not minding the stream of cum. </p><p>“ I do… I feel like a girl, Sir…” She said, sounding exhausted. </p><p>“Do you want to do this again next week?” He asked, patting her cheek so she would be awake for that last question…</p><p>…</p><p>“Yeah… I’d like to do this again…” She mumbled, before finally falling asleep…</p>
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